[Background] Selecting an appropriate task is challenging for Open Source Software (OSS) project newcomers and a variety of strategies can help them in this process. [Aims] In this research, we compare the perspective of maintainers, newcomers, and existing contributors about the importance of strategies to support this process. Our goal is to identify possible gulfs of expectations between newcomers who are meant to be helped and contributors who have to put effort into these strategies, which can create friction and impede the usefulness of the strategies. [Method] We interviewed maintainers (n=17) and applied inductive qualitative analysis to derive a model of strategies meant to be adopted by newcomers and communities. Next, we sent a questionnaire (n=64) to maintainers, frequent contributors, and newcomers, asking them to rank these strategies based on their importance. We used the Schulze method to compare the different rankings from the different types of contributors. [Results] Maintainers and contributors diverged in their opinions about the relative importance of various strategies. The results suggest that newcomers want a better contribution process and more support to onboard, while maintainers expect to solve questions using the available communication channels. [Conclusions] The gaps in perspectives between newcomers and existing contributors create a gulf of expectation. OSS communities can leverage our results to prioritize the strategies considered the most important by newcomers.